Hydrochloric Acid → 3-Iodo-4-methylthiophene-2-carboxylic acid

HRID 422580Notes

Reaction equation

HRID 422580 reaction equation
[I:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([O:10]C)=[O:9].[OH-].[Na+].CO.Cl>C1COCC1>[I:1][C:2]1[C:6]([CH3:7])=[CH:5][S:4][C:3]=1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 2761204Methyl 3-iodo-4-methylthiophene-2-carboxylate

Product 1

HCID 27613913-Iodo-4-methylthiophene-2-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-iodo-4-methylthiophene-2-carboxylate [Oakwood Product Inc.] (10 g, 35.4 mmol) in THF (200 mL) was added a solution of 2N NaOH (19.50 mL, 39.0 mmol). MeOH was added to the reaction mixture until a homogeneous solution was obtained. After about 4 h, concentrated HCl was added until a pH of about 1 was obtained. The reaction mixture was partially concentrated under reduced pressure and the resulting solid was collected by filtration and dried under reduced pressure to provide the title compound as a brown solid (9.50 g, 100%): LC/MS (Table 1, Method a) Rt=2.55 min; m/z: 267 (M−H)−.

Workup

  1. customwas obtained
  2. customwas obtained
  3. concentrationThe reaction mixture was partially concentrated under reduced pressure
  4. filtrationthe resulting solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-2ab90379767a459f929aa5959fa81b6a
Source dataset
uspto-grants-2012_01
Patent number
US08101645B2

Reaction notes

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